US1644850A - Manufacture of isodibenzanthrones - Google Patents

Manufacture of isodibenzanthrones Download PDF

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Publication number
US1644850A
US1644850A US87167A US8716726A US1644850A US 1644850 A US1644850 A US 1644850A US 87167 A US87167 A US 87167A US 8716726 A US8716726 A US 8716726A US 1644850 A US1644850 A US 1644850A
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United States
Prior art keywords
isodibenzanthrones
benzanthrone
manufacture
free
parts
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Expired - Lifetime
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US87167A
Inventor
Neresheimer Heinrich
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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Publication date
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups

Definitions

  • a mixture of 17.6 parts of benzanthrone- Bz l-thioaracresyl-ether corresponding to the formu a and 11.5 parts of benzanthrone are introduced into a solution of parts of sodium in 500 parts of water-free ethyl alcohol -heated to about 105 to 110 degrees centigrade while distilling off part of the alco- 49 hol, and kept at the said temperature for some hours while stirring.
  • the isodibenzanthrone so prepared can be separated and purified in the usual manner. It is obtained rically or asymmetrically substitute in a considerably better yield and, owing to the use 1n part of simple benzanthrone, 5

Description

Patented Oct. 11, 1927. 1
UNITED STATES PATENT OFFICE.
-TO I. G.
FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT-ON-THE- MAIN, GERMANY, A CORPORATION OF GERMANY.
MANUFACTURE OF ISODIBENZANTHRONES.
No Drawing. Application filed February 9, 1926, Serial No. 87,167, and in Germany February 16, 1925.
I have found'that isodibenzanthrones can be prepared in an advantageous manner by treating mixtures of B2 l-benzanthrone-thioethers and benzanthrones not substituted in 5 the B2 1position both components having a free 2-position with alkaline condensing agents. Generally, about equimolecular quantities of the two components will be employed, but the process is not limited to a certain proportion of the components. Mixtures of caustic alkalis with alcohols are especially suitable as condensing agents. It is advantageous to exclude oxygen during the condensation as far as possible, for
example by introducing an inert or reducmg gas.
The following example will further illustrate my invention which, however, is not limited to this example. The parts are by weight.
Emample.
A mixture of 17.6 parts of benzanthrone- Bz l-thioaracresyl-ether corresponding to the formu a and 11.5 parts of benzanthrone are introduced into a solution of parts of sodium in 500 parts of water-free ethyl alcohol -heated to about 105 to 110 degrees centigrade while distilling off part of the alco- 49 hol, and kept at the said temperature for some hours while stirring. The isodibenzanthrone so prepared can be separated and purified in the usual manner. It is obtained rically or asymmetrically substitute in a considerably better yield and, owing to the use 1n part of simple benzanthrone, 5
at a lower cost than when treating benzan- (see Scholl, Ber. d. Deutschen Chem. Gesellsch., vol. 55, p. 114) a mono-chlor-isodibenzanthrone is obtained. Other s mmti: 1so benzanthrones may be prepared in an analogous way.
What I claim is:
1. The process of manufacturing isodibenzanthrones which consists in treating a mixture of a benzanthrone-Bz l-thio-ether having a free 2-position and a benzanthrone with free 2- and Bz l-positions with an alkaline condensing agentsubstantially in the absence of oxygen.
2. The process of manufacturing isodibenzanthrones which consists in treating a mixture of about equimolecular proportions of a benzanthrone-Bz l-thio-ether having a free 2-position and a benzanthrone with free 2- and Bz l-positions with an alkaline con- 30 densing agent substantially in the absence of oxygen.
In testimony whereof I have hereunto set my hand.
HEINRICH NERESHEIMER.
EERTKFHGATE 0h CURRECTIGN.
Patent No. L64 2q85ii, Granted (Detober 11, 1927, to
HEENR ii (Si-i NERESHEIMER.
It is hereby certiiieti that the above numbered patent wee erroneously issued to "l. G. Farhenindnstrie Aktiengeseiischei't, of Frankiort=on-the-Main, Gertnnny a Uorporation oi Germany", whereas said patent should have been issued to "Gresseiii Dyeetnfi Corporation, oi New York N. Y., a Corporation of Delawere" saioi Corporation being nssignee by mesne assignments of the entire interest in said? invention, as shown by the records of assignmentsin this office; and that the said Letters Patent shoniri be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 8th day of November, A. D. 1927.
" Ma Moore,
Seal. Acting Commissioner oi Pntenten
US87167A 1925-02-16 1926-02-09 Manufacture of isodibenzanthrones Expired - Lifetime US1644850A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1644850X 1925-02-16

Publications (1)

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US1644850A true US1644850A (en) 1927-10-11

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